Holiday rentals with breakfast in West Ashley, Charleston

Home in Cannonborough/ Elliottborough

4.85 out of 5 average rating, 316 reviews

Trendy Downtown Upper King Area~Rutledge Retreat B

In the emerging area known as Cannonborough/Elliotborough. Built in the 1800's but all modern conveniences. In renting this newly renovated 2 bedroom apt you will find yourself within blocks of historic parks, sites, stores, restaurants, bars & all that the revitalized Upper King has to offer. NOTE: This is a 2 person/1 BDRM Booking Rate with full, private use of all common spaces with one BRM blocked. A $25 per person, per day for all persons over 2 includes use of both BRMS. Sleeps 1-4 people.

4.87 out of 5 average rating, 161 reviews

Family Home~Walkable to Park Circle~Short drive DT

✨ Welcome to The Delsey ✨ Enjoy your stay in North Charleston’s beloved Park Circle neighborhood at this charming 1928 cottage — lovingly updated with modern touches while preserving its historic soul. 🏡 📍 Just one block from Park Circle’s main strip w/ amazing restaurants, breweries, & shops! 🚗 10 min to the Coliseum & CHS Airport 🌆 20 min to Downtown CHS 🏖️ 30 min to the beach Whether you're here for a weekend getaway, concert, or Lowcountry adventure, this is the perfect home base! 🌴

Guest house in Summerville

4.98 out of 5 average rating, 703 reviews

★Delightful guest house near historic plantations★

Nestled in the Historic Plantation District between Summerville & Charleston, our timberframe "bunkhouse" offers privacy, comfort & convenience. This 850+ sq ft retreat includes full kitchen & bath, 2 dbl beds, twin bed & plenty of living space. There's a private entrance, so come & go as you please (we're right next door if you need us). Minutes from Middleton Place, Drayton Hall & Magnolia Gardens, an easy drive to dntn Charleston, historic S'ville, beaches & golf courses. *Now with WiFi*

4.98 out of 5 average rating, 132 reviews

Cottage in James Island

Southern Cottage between downtown and beaches

Newly renovated cozy cottage provides the Low Country experience you & your family are looking for. Enjoy Riverland Terrace, a quiet & hospitable neighborhood centrally located in Charleston. Only a short 10 min drive to downtown, 15 min to Folly Beach, & 20 min from the Charleston International Airport. Kitchen is fully stocked, the coffee bar includes coffee and Nespresso pods. Grocery stores within 2 miles. Comfortable King, Queen, Full & 2 twin beds. Free parking, fast wifi, pet friendly.

5 out of 5 average rating, 31 reviews

•Charleston Cottage• central to Airport & Downtown

Welcome to our charming 3-bedroom, 1-bath home nestled in the heart of Park Circle, North Charleston! Whether you’re visiting for a family vacation, a romantic getaway, or a business trip, our home offers the perfect blend of comfort and convenience. Centrally located, Park Circle is just minutes from North Charleston’s best dining, shopping, and entertainment. With downtown Charleston’s historic charm and beaches a short drive away, our home is the perfect base for exploring the Lowcountry.

Guest suite in West Ashley

4.99 out of 5 average rating, 379 reviews

The Garden Folly Guest House

Our architect said, “this is NOT a garage, it’s a Garden Folly!” Our Guest House has a bird’s eye view of the rose covered pecan tree and a vista of the marsh and the Wappoo Creek. When we rebuilt our 1930's garage we saved all the beaded siding and pine floor. My husband enjoyed incorporating many design elements and creative ideas. It was quickly becoming the Taj Garage. We decided it was just the kind of property we enjoy when we travel, so, Voila! we decided to share it with you!

4.91 out of 5 average rating, 125 reviews

Katie's House

Open concept, living room, dining, fully stocked kitchen 3 bedrooms 2 baths, screened backporch, washer/dryer, self-check in. Outdoor security cameras. Central heating/air. Fast Wi-Fi. The house is a smart home with smart TVs, radio/CD player. CVS next door, dog park behind CVS. Airport 12 min, Amtrak 3 min Tanger outlet/Walmart/Sam's Club 8 min, downtown Charleston 17 min Beaches 20-30 min. Restaurants, Old North Charleston 3 min. North Charleston Short-Term Rental Permit 2025-0583

4.97 out of 5 average rating, 143 reviews

Cottage in Johns Island

Pet Stay Free, Near Charleston and Kiawah!

This is an all outdoors vacation experience! Nature entertains you like a moving picture of your daily life. Relax in a private corner of our farm. Fish, paddle board, canoe, hike trails, watch horses, & bird watch. Or have a quiet dinner in our cozy space with a full kitchen. Bring your bikes to ride our trails. Once you book with us, a Grocery service is just a click away so your kitchen will be stocked with all your requests before your arrival. 2 pets allowed. ZSTR012501107

Guest house in West Ashley

4.9 out of 5 average rating, 626 reviews

Cozy Cottage w Games, Firepit, Grill, and More!

Centrally located cottage perfect for exploring the wonders of Charleston! - Amazing location; quick drive to downtown, minutes from Avondale, 12 miles to Folly Beach. - On a beautiful 9 mile bike & walking path - Backyard oasis with games, firepit, grill, and outdoor dining space - Beach chairs, cooler, and umbrella available - Updated interiors with king bed, games, streaming, and fast wifi Enjoy the perfect home base to explore the Lowcountry. We can't wait to host you!

Superhost

Tiny home in James Island

4.83 out of 5 average rating, 409 reviews

The Cashmere Guest Suite - PERFECT LOCATION!

SANITIZED THOROUGHLY BETWEEN GUESTS! Luxury private suite behind an historic home, the Cashmere Cottage is located in beautiful, Live Oak-filled Riverland Terrace - less than 3 miles from downtown & 8 miles from Folly Beach. You'll feel like royalty in this condensed space with luxury linens, fully ADJUSTABLE BED (!!), plush towels & robes, coffee bar with mini-fridge, & huge bathroom with a gorgeous frameless shower & salon-quality products to pamper yourself.

4.95 out of 5 average rating, 134 reviews

Home in North Charleston

The Artist: cute and easy drive to downtown

This 2 bedroom 1 bathroom house is small but mighty! 🎨Incredibly cute curated space 🌳huge fenced in back yard 🍍minutes to downtown 🏝️25 minutes to beaches like Sullivan's Island 🌞fun + cozy porch area 🏡 at the end of a dead end street for extra privacy Perfect for your weekend getaway to Charleston. Located in North Charleston, minutes from everywhere worth going. PAC/Coliseum, Riverfront Park, Downtown, the beaches, just to name a few.